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This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This file focusses on teaching staff photographs, since John Buchanan's headmastership. More recent photographs include both teaching and support staff.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

A group of photographs of the interior of Old School, including some of the frescoes, and a letter regarding Mary Sargant Florence's life and work.

A list of the Friends of the Festival. Two pages A and B.

A list of the names and addresses of the organisers of the 1993 Oakham Festival.

This file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

This series gathers various correspondence regarding the Chapel throughout the years.